Pd(II)-Catalyzed ortho-Trifluoromethylation of Arenes Using TFA as a Promoter

被引:456
作者
Wang, Xisheng [1 ]
Truesdale, Larry [2 ]
Yu, Jin-Quan [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Pfizer Inc, La Jolla Labs, Dept External R&D Innovat, San Diego, CA 92121 USA
基金
美国国家科学基金会;
关键词
MEDICINAL CHEMISTRY; ORGANIC HALIDES; BOND FORMATION; PALLADIUM; FLUORINE; PD; COMPLEXES; ALDEHYDES; ALKYNES; AGENTS;
D O I
10.1021/ja909522s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Pd(II)-catalyzed C-H activation/trifluoromethylation of arenes with an electrophilic trifluoromethylation reagent using diverse heterocycle directing groups is reported. The presence of trifluoroacetic acid is crucial for this catalytic reaction.
引用
收藏
页码:3648 / +
页数:4
相关论文
共 32 条
[1]  
[Anonymous], ADV ORGANOMET CHEM
[2]  
Chen Q.-Y., 1989, CHEM COMMUN, P705
[3]   Synthetic and Mechanistic Studies of Pd-Catalyzed C-H Arylation with Diaryliodonium Salts: Evidence for a Bimetallic High Oxidation State Pd Intermediate [J].
Deprez, Nicholas R. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :11234-11241
[4]   Active trifluoromethylating agents from well-defined copper(I)-CF3 complexes [J].
Dubinina, Galyna G. ;
Furutachi, Hideki ;
Vicic, David A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) :8600-+
[5]   Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes [J].
Gevorgyan, V ;
Quan, LG ;
Yamamoto, Y .
TETRAHEDRON LETTERS, 1999, 40 (21) :4089-4092
[6]   Facile Ar-CF3 bond formation at Pd.: Strikingly different outcomes of reductive elimination from [(Ph3P)2Pd(CF3)Ph] and [(Xantphos)Pd(CF3)Ph] [J].
Grushin, Vladimir V. ;
Marshall, William J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12644-12645
[7]   The Organometallic Fluorine Chemistry of Palladium and Rhodium: Studies toward Aromatic Fluorination [J].
Grushin, Vladimir V. .
ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (01) :160-171
[8]   The many roles for fluorine in medicinal chemistry [J].
Hagmann, William K. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4359-4369
[9]   Palladium-catalyzed fluorination of carbon-hydrogen bonds [J].
Hull, Kami L. ;
Anani, Waseem Q. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) :7134-7135
[10]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS BETWEEN ALLYL, VINYL OR ARYL HALIDE AND PERFLUOROALKYL IODIDE WITH ZINC AND ULTRASONIC IRRADIATION [J].
KITAZUME, T ;
ISHIKAWA, N .
CHEMISTRY LETTERS, 1982, (01) :137-140